Work

Introduction of the Difluoro(methoxy)methyl Group into the Aromatic Ring and the Study of Its Electronic Properties

Year: 2024

Type: article

Abstract: A simple and efficient method for synthesizing aromatic compounds with a difluoro(methoxy)methyl fragment (CF2OCH3) by the fluorodesulfurization of thionoesters has been developed. Systematic screening identified SnCl4/DAST as the optimal reagent combination, providing excellent selectivity and high yields of target products. A series of aromatic difluoro(methoxy)methyl compounds was synthesized under these conditions. Further studies of the electronic properties of the difluoro(methoxy)methyl group using 19F NMR allowed us to determine its Hammett constants for inductive (σI) and resonance (σR) effects. The results show that CF2OCH3 acts as a moderately electron-withdrawing substituent, underscoring its potential as a versatile group for designing organic molecules with precisely tuned electronic characteristics.

Source: Journal of organic and pharmaceutical chemistry

DOI: 10.24959/ophcj.24.321167

Authors: Mykhailo O. Pashko, Yurii L. Yagupolskii

Institutions: National Academy of Sciences of Ukraine, Institute of Organic Chemistry

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: diamond

OpenAlex ID: W4409216099

FWCI:

Cites: 14

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Related to: 10